Indole-3-acetamides: As Potential Antihyperglycemic and Antioxidant Agents; Synthesis, In Vitro α-Amylase Inhibitory Activity, Structure–Activity Relationship, and In Silico Studies
| Autor: | Khalid Mohammed Khan, Munissa Younus, Huma Khan, Shahnaz Perveen, Muhammad Taha, Kanwal, Sridevi Chigurupati, Abdul Wadood, Maha A Aldubayan, Farman Ali |
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| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Indole test ABTS Antioxidant biology DPPH General Chemical Engineering medicine.medical_treatment Active site General Chemistry Article Addition/Correction Chemistry chemistry.chemical_compound Enzyme chemistry biology.protein medicine Structure–activity relationship Amylase QD1-999 Nuclear chemistry |
| Zdroj: | ACS Omega ACS Omega, Vol 6, Iss 3, Pp 2264-2275 (2021) |
| ISSN: | 2470-1343 |
| DOI: | 10.1021/acsomega.0c05581 |
| Popis: | Indole-3-acetamides (1–24) were synthesized via coupling of indole-3-acetic acid with various substituted anilines in the presence of coupling reagent 1,1-carbonyldiimidazole. The structures of synthetic molecules were elucidated through different spectroscopic techniques including electron ionization-mass spectroscopy (EI-MS), 1H-, 13C NMR, and high-resolution EI-MS (HREI-MS). These compounds were screened for their antihyperglycemic and antioxidant potentials. All compounds displayed good to moderate inhibition against α-amylase enzyme with IC50 values ranging between 1.09 ± 0.11 and 2.84 ± 0.1 μM compared to the standard acarbose (IC50 = 0.92 ± 0.4 μM). Compound 15 (IC50 = 1.09 ± 0.11 μM) was the most active compound of the series and exhibited good inhibition against α-amylase; in addition, this compound also exhibited good antioxidant potential with IC50 values of 0.35 ± 0.1 and 0.81 ± 0.25 μM in 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays, respectively. The binding interactions of synthetic molecules with the enzyme’s active site were confirmed via in silico studies. The current study had identified a number of lead molecules as potential antihyperglycemic and antioxidant agents. |
| Databáze: | OpenAIRE |
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